(1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one | 321199-81-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one
• 英文别名: (2R,4S,5R)-4-hydroxy-2-methyl-5-(6-methylhepta-1,5-dien-2-yl)cyclohexan-1-one
• CAS: 321199-81-9
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: QCVXGVVLXAANDD-NFAWXSAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 氢氟酸 作用下， 以 乙腈 为溶剂， 以80%的产率得到(1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one
  参考文献：
  名称：

  Synthesis and stereochemical determination of an antifeeding bisabolanoid from Japanese cedar

  摘要：

  The first enantioselective synthesis of (1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one, a potent antifeedant isolated from the Japanese cedar. Cryptomeria japonica, was achieved starting from methyl (R)-4-hydroxy-3-methylbutanoate via a stereoselective carbonyl ene cyclization reaction as the key step. Comparison of the spectral data and specific rotation of the synthetic material with those of the natural product led to unambiguous stereochemical assignment of the antifeedant as 1S, 3R, and 6R. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.039

文献信息

• Syntheses of Bioactive Bisabolane-Type<i>Cryptomeria japonica</i>Sesquiterpenes
  作者：Nobuhiro SHIMIZU、Yasumasa KUWAHARA

  DOI：10.1271/bbb.80671

  日期：2009.3.23

  The first diastereoselective synthesis of (1S,6R)-1-hydroxy-2,7(14),10-bisabolatrien-4-one, an antifeedant against Acusta despesta and Locusta migratoria, was produced from Cryptomeria japonica (commonly known as Japanese cedar), starting from (R)-(−)-carvone via (R)-(−)-cryptomerione. The enantiomer was transformed into (1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one, a novel antifeedant against L. migratoria from the same tree, by 1,4-selective reduction of the enone moiety.

  首次非对映选择性合成了(1S,6R)-1-羟基-2,7(14),10-双abolatrien-4-酮，它是一种针对Acusta despesta和Locusta migratoria的抗飞虫剂，合成是从日本雪松（俗称日本杉）开始，通过(R)-(-)-cryptomerione合成(R)-(-)-carvone。通过烯酮分子的 1,4 选择性还原，该对映体被转化为(1S,3R,6R)-1-羟基-7(14),10-双羟基二烯-4-酮，这是一种从同一树种中提取的新型移虫抗药性。